Re: ORGLIST: chlorosulfation

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From: Jay (hi_buddy03$##$yahoo.com)
Date: Wed Jan 10 2007 - 08:43:49 EST


I am using THF as the mobile phase for HPLC so I wonder if the compound is still getting hydrolyzed. Also, if there is a better way to monitor this reaction please let me know.
  I am using this reaction to incorporate the SO2 group so the final strucutre after this reaction would be Ar-CH2-O-SO2Cl
  The next step I want to try is to substitute the Cl group.
   
  Regards,
  Jay

Andrew Lund <android109$##$hotmail.com> wrote:
  
Is it possible that what's happening is that the sulfuryl chloride is chlorinating the alcohol and then under the HPLC conditions this is hydrolysing back to the starting alcohol? Sulfuryl chloride is very reactive and I'd expect it toi react immediately with the alcohol. Is the chlorosulfonate the final target or is it simply an activated intermediate where perhaps mesylate might be a better choice...?
Andy

________________________________
> Date: Mon, 8 Jan 2007 14:29:34 -0800
> From: hi_buddy03$##$yahoo.com
> To: everybody$##$orglist.net
> Subject: ORGLIST: chlorosulfation
>
> Hello all,
> I am trying to perform a chlorosulfation reaction as an intermediate step.
> The reaction is as follows:
> Ar-CH2OH + SO2Cl2 --------> Ar-CH2OSO2Cl
> (3 mol) (3.6mol)
> Toluene as solvent and pyridine as a base.
> I am monitoring this reaction on HPLC but I cannot see anything other than the starting material peak.
> I thought SO2Cl2 being very reactive would give the product easily.
> I need some feedback on as to whether the method that I am using for synthesis has flaws or the reaction monitoring method is incorrect?
> If anybody has a new approach to this synthesis should also be fine.
> Thanks,
> Jay
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